New Class of Anionic Cascade Reactions for Organic Synthesis

NSF化学部的化学合成计划支持亚利桑那大学化学和生物化学系Jon T.Njardarson教授的研究。杂环化合物是药物中最重要的结构支架之一，在许多其他材料应用中也发挥着关键作用。Njardarson教授和他的学生开发了有用的新的级联反应来制造药物。对于这些新的级联反应中的每一个，两个简单且容易获得的构建块以一种方式结合在一起，从而产生有价值的复杂的手性产物。此外，该项目还为本科生和研究生提供了出色的培训。与这些项目相关的学生参与的特别值得注意的交付成果是独特的免费获取的教育/研究工具，例如用于结构阐明的教学工具、免费的移动应用程序/网站设计的化学和新颖的药物结构分析。在该奖项中开发的新杂环方法为制药业的研究人员提供了构建重要结构的新的和补充的方法。通过使用级联反应，研究人员在a)阴离子异构化、b)阴离子加速重排、c)扩环反应、d)应变辅助重排和e)不对称偶极环加成反应领域建立了新的知识，同时在有价值的杂环结构的不对称合成方面做出了创新贡献。这一研究项目产生的许多反应为学术界和工业界的研究人员为他们的目标导向合成追求开发有用的新蓝图打开了大门。这些使用双官能亲核试剂的新型反应有望具有广泛的范围和高度的可调性。特别侧重于阐明和理解反应机理，以便由此产生的知识基础可以帮助设计新的反应和开辟新的研究途径。这些新的教育产品为学生、研究人员和公众提供了新的机会来了解有机化学及其对社会的重要性。

The Chemical Synthesis Program of the NSF Chemistry Division supports the research of Professor Jon T. Njardarson in the Department of Chemistry and Biochemistry at the University of Arizona. Heterocyclic compounds are one of the more important structural scaffolds found in pharmaceuticals while also playing key roles in numerous other material applications. Professor Njardarson and his students develop useful new cascade reactions to make pharmaceuticals. For each one of these new cascade reactions, two simple and readily accessible building blocks are brought together in such a way that valuable complex chiral products result. In addition, this project provides excellent training of undergraduate and graduate students. Particularly noteworthy deliverables, which the students associated with these projects are involved in, are unique freely accessible educational/research tools such as pedagogical tools for structure elucidation, the free mobile app/website Chemistry By Design and, novel pharmaceutical structure analyses. The new heterocyclic methods developed in this award provide researchers in the pharmaceutical industry with new and complementary approaches for building important structures. Through the use of cascade reactions, the researchers make innovative contributions to the asymmetric syntheses of valuable heterocyclic ring structures while establishing new knowledge in the areas of a) anionic isomerizations, b) anion accelerated rearrangements, c) ring expansion reactions, d) strain assisted rearrangements, and e) asymmetric dipolar cycloaddition reactions. The many reactions emerging from this research program open the door for researchers in academia and industry to develop useful new blueprints for their target oriented synthesis pursuits. These new classes of reactions, which employ bi-functional nucleophiles, promise to be of broad scope and highly tunable. Particular focus is on elucidating and understanding the reaction mechanisms so that the resulting knowledge foundation can aid in designing new reactions and opening new avenues of investigation. These new educational products provide students, researchers and the public with new opportunities to learn about organic chemistry and its importance to society.